New to the island, and wondering where the best area to stay in Key West, FL, is?
For a small dot on the ocean, Key West has a surprising number of neighborhoods and sections. There are different vibes for different folks, but generally, the various neighborhoods to stay in Key West are all good picks for visitors. Here’s a guide to where to stay in Key West and a brief intro into how our island home is laid out.
Neighborhoods and Places to Stay in Key West
First, while many Mainlanders refer to our island as simply “Key West,” locals use a more nuanced approach. Just like you might think of your friend as being from New York, but they say they’re from the Upper East Side.
So, here are the parts of Key West you might read or hear about. Keep in mind that these sections of town don’t have official boundaries, so different people may draw their maps differently. It’s a free country like that.
Old Town Key West
Old Town might be considered downtown, with world-famous Duval Street being ‘Main Street.’ It occupies most of the island’s west side, encompassing most everything west of White Street. Inside Old Town are a few different neighborhoods you might hear about, like the Truman Annex, Bahama Village, and Casa Marina. The area around Duval is sometimes called the “Heart of Old Town.” As the name suggests, Old Town is where the island was first settled, generally around the harbor.
Old Town may be the best area to stay in Key West, Florida, simply because it’s central to everything: Duval Street is the island’s epicenter, ground zero for everything from festivals and live music to about a zillion bars and the best restaurants in Key West.
Most of Key West’s best B&Bs and resorts are sprinkled around Old Town. There are huge resorts on Duval and the harbor, like La Concha, Opal Key, Pier House, and Ocean Key resorts. Honestly, there are too many to list, but some of the best places to stay in Key West Old Town include:
- 24 North
- Havana Cabana
- The Gates Hotel
- Private homes on VRBO and Airbnb
Stock Island, Key West’s Neighbor
Stock Island isn’t on Key West at all, but it’s the next island immediately to its east. Many locals live on this residential island since it’s only a few minute’s drive into New Town, Midtown, or Old Town. And even though it’s not technically in Key West, Stock Island is actually one of the best areas to stay in Key West!
Stock Island has a rustic feel that some say is like “Old Key West.” They don’t mean that it’s like Old Town; they mean that it’s something like Key West used to be — it’s quieter, more residential, and a little less polished and ‘touristy.’ It makes a nice, relaxed place to stay for a vacation, but keep in mind that it is pretty far from Old Town. You’ll want to get a shuttle or Uber to and from downtown.
However, Stock Island has a few new, shiny resorts. Check out The Perry Hotel and Ocean’s Edge Resort—both are TripAdvisor top picks and highly rated. Also, a few houses are on Airbnb.
I think Stock Island is the best location to stay in Key West when visiting, but then I’m a little biased. If you book a private Key West sandbar tour with us, you’ll find out — I keep the Casual Monday docked on Stock Island for a reason!
Where’s the Best Place to Stay in Key West?
It’s probably apparent by now that where to stay in Key West has a lot to do with what you want to do when you get here. There are tons of different neighborhoods and places to stay in Key West, but finding one that suits your vacation isn’t that hard. Sometimes it’s about cost, and sometimes it’s about convenience. Many folks want to park their cars and spend their time walking around Old Town, which is precisely why it’s usually the best area to stay in Key West, FL.
But if you’re more into visiting the Lower Keys and want to have a little more mobility to get on and off the island, New Town or Stock Island make solid choices. And, in the end, you’re in the Keys, the sun is shining, and the nearest margarita is usually only a few steps away.
No matter where you stay in Key West, visit me on Stock Island and book a private boat tour of Key West’s best beaches.
- Southernmost Beach Resort
- Key West Harbor Inn
- H2O Suites
- The Marker
- The Gardens
The Meadows
The Meadows is a tiny little neighborhood on the island’s north end just off the Navy base. It’s close to the Key West port and only about a 20-minute walk to Duval. It’s an exclusive neighborhood with large homes and tree-lined streets.
There are a few motels and inns along the marina, but your best bet if you want to stay in The Meadows is to grab a vacation rental off Airbnb or VRBO.
Midtown Key West
Midtown stretches from White Street eastward toward the airport. Some people divide it into Midtown East and Midtown West, which seems a bit cheeky to me. This part of town is primarily residential, with a more modern and suburban feel than Old Town—bigger yards and modest, mid-century homes. It’s not far into Old Town from here, but most people choose to bike or take an Uber.
Midtown is an excellent choice for visitors if they don’t want to be in the middle of the party but still want to be within easy access to restaurants and the beach. On the island’s south side, Midtown includes some of the best Key West beaches, like Higgs and Smathers; that’s why this part of town is sometimes called Beachside.
Some options in Midtown Key West include the Margaritaville Beach House and 1800 Atlantic condos. Plus, this is a good place to find a deal on a vacation rental if you want to get a whole house for privacy during your stay.
New Town
If there’s an Old Town, there must be a New Town, right?
New Town is the area you first drive through when you come on the island. It’s all the land on the island’s east end, including everything around the airport. Where New Town ends and Midtown begins is fuzzy. The houses in New Town are, well, newer: they feel like typical Florida homes with larger lots and more luxurious structures.
New Town is much farther from Duval and the island’s hot spots than the other neighborhoods. The north end of New Town, along Roosevelt Blvd., is where you’ll find the island’s supermarkets, chain stores, and fast food. There are also some chain hotels here,
This is a good part of town to visit if you’re looking to stay in the Lower Keys but want to drive around and explore — it’s quick to get out of town and head north on US 1, but it’s also possible to drive into Old Town and park. However, it’s always best to get a ride share or park a ways out and walk. Parking is sometimes hard to come by in Old Town!
There are a few hotels in New Town, mostly along North Roosevelt Blvd.
- 24 North
- Havana Cabana
- The Gates Hotel
- Private homes on VRBO and Airbnb
Stock Island, Key West’s Neighbor
Stock Island isn’t on Key West at all, but it’s the next island immediately to its east. Many locals live on this residential island since it’s only a few minute’s drive into New Town, Midtown, or Old Town. And even though it’s not technically in Key West, Stock Island is actually one of the best areas to stay in Key West!
Stock Island has a rustic feel that some say is like “Old Key West.” They don’t mean that it’s like Old Town; they mean that it’s something like Key West used to be — it’s quieter, more residential, and a little less polished and ‘touristy.’ It makes a nice, relaxed place to stay for a vacation, but keep in mind that it is pretty far from Old Town. You’ll want to get a shuttle or Uber to and from downtown.
However, Stock Island has a few new, shiny resorts. Check out The Perry Hotel and Ocean’s Edge Resort—both are TripAdvisor top picks and highly rated. Also, a few houses are on Airbnb.
I think Stock Island is the best location to stay in Key West when visiting, but then I’m a little biased. If you book a private Key West sandbar tour with us, you’ll find out — I keep the Casual Monday docked on Stock Island for a reason!
Where’s the Best Place to Stay in Key West?
It’s probably apparent by now that where to stay in Key West has a lot to do with what you want to do when you get here. There are tons of different neighborhoods and places to stay in Key West, but finding one that suits your vacation isn’t that hard. Sometimes it’s about cost, and sometimes it’s about convenience. Many folks want to park their cars and spend their time walking around Old Town, which is precisely why it’s usually the best area to stay in Key West, FL.
But if you’re more into visiting the Lower Keys and want to have a little more mobility to get on and off the island, New Town or Stock Island make solid choices. And, in the end, you’re in the Keys, the sun is shining, and the nearest margarita is usually only a few steps away.
No matter where you stay in Key West, visit me on Stock Island and book a private boat tour of Key West’s best beaches.
